Synthetic study of 1,3-butadiene-based IMDA approach to construct a [5-7-6] tricyclic core and its application to the total synthesis of C8-epi-guanacastepene O

Chuang-Chuang Li; Cui-Hua Wang; Bo Liang; Xin-Hao Zhang; Lu-Jiang Deng; Shuang Liang; Jia-Hua Chen; Yun-Dong Wu; Zhen Yang

doi:10.1021/jo060996h

Synthetic study of 1,3-butadiene-based IMDA approach to construct a [5-7-6] tricyclic core and its application to the total synthesis of C8-epi-guanacastepene O

J Org Chem. 2006 Sep 1;71(18):6892-7. doi: 10.1021/jo060996h.

Authors

Chuang-Chuang Li¹, Cui-Hua Wang, Bo Liang, Xin-Hao Zhang, Lu-Jiang Deng, Shuang Liang, Jia-Hua Chen, Yun-Dong Wu, Zhen Yang

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering , Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Shenzhen Graduate School, Peking University, Beijing 100871, China.

PMID: 16930042
DOI: 10.1021/jo060996h

Abstract

An efficient intramolecular Diels-Alder (IMDA) strategy for the construction of the [5-7-6] tricyclic core (18) of guanacastepenes has been developed from cis- and trans-1,3-butadiene-tethered 4-oxopent-2-ynoic acid ethyl esters 10 and 11. This method facilitates the synthesis of C8-epi-guanacastepene O (36) in a very efficient manner.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Butadienes / chemistry*
Chemistry, Organic / methods*
Crystallography, X-Ray
Diterpenes / chemical synthesis
Diterpenes / chemistry
Ketones / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure

Substances

Butadienes
Diterpenes
Ketones
guanacastepene
1,3-butadiene